What Is It Like to Live in Downtown Naples, Near Fifth Avenue South?

It means your evening can start with a walk instead of a drive. Downtown Naples centers on Fifth Avenue South and Third Street South, two walkable streets in Old Naples lined with restaurants, galleries and shops you will not find in a strip center. Live a few blocks away and dinner, a gallery opening or an ice cream after sunset at the beach are all on foot.

I am Kris Asquith, Broker Associate at Premiere Plus Realty, and I help buyers and sellers in Naples and eight other Southwest Florida markets. When someone tells me they want to be able to walk to dinner, this is the part of Naples I show them first.

It is a real street, not a mall. Fifth Avenue South is the closest thing on this coast to a proper dining street: tables on the sidewalk, independent shops and galleries, and evening life that keeps going after the stores close. It sits right in the middle of Old Naples, so the homes around it are part of the neighborhood rather than a drive away from it.

Third Street South is a few blocks over. It is quieter and older, with courtyards tucked behind the shops and a farmers market on Saturday mornings. A lot of locals will tell you it is their favorite of the two. Living between them means you get both.

One of my favorite tables downtown is at Truluck's, the seafood and steak house at 698 4th Avenue South. It sits on 4th Avenue South, a block off Fifth, and it has been downtown since 2004.

Here is how I order. I start with the Voilà! cocktail, which comes to the table smoking. Then the shrimp cocktail, a filet, and the Baked Alaska to finish, which they set on fire right at the table. It is a fun night, and it never feels rushed.

Truluck's is one of many good tables within a short walk of each other. My guide to where to eat across Southwest Florida lists more of my picks in Naples and beyond. Hours change with the season, so call ahead before you go: Truluck's Naples is at (239) 530-3131.

More than people expect. From January through April, downtown is full. You book dinner ahead, even on a weeknight, parking takes longer, and the sidewalks are busy until late. That energy is a big part of why people love living here.

From June through September, it is a different town. The same restaurants are easy to walk into, a few take a short break or trim their days, and the ones that stay open are a pleasure. People here also eat early, so a place that is busy at half past five can be calm by eight.

If you are deciding whether downtown is right for you, try to see it in both seasons. Someone who only visits in February can be surprised by a quiet August, and the reverse is just as true.

Old Naples itself surrounds the two streets, with a mix of single-family homes, townhomes and condos on quiet, tree-lined blocks. South of downtown, Aqualane Shores sits on Naples Bay with wide deep-water canals and private docks, and it is within walking distance of Third Street South and Fifth Avenue South. Farther down, Port Royal fills the southern tip of Naples, with curving deep-water canals and no bridges between the dock and the Gulf.

If you want to lock the door and leave for the summer, a condo near downtown is worth a look. My page on condos in Naples covers what to check in a building before you buy, including the inspection and reserve study reports Florida now requires for many condo buildings.

For the right person, yes. Being able to walk to Fifth Avenue South and Third Street South is built into what homes in Old Naples are worth, and it is one of the reasons buyers ask for this area by name. You trade a bigger yard or a gated entrance for a neighborhood where you know the people at the coffee shop and leave the car parked most evenings.

The best way to know is to spend a day here like a resident. Walk to breakfast, browse the shops, catch the sunset at the beach, then walk to dinner. If that day feels like home, downtown is probably your place.

Start with a search for the streets you would actually walk. You can set up a home search by area, price and must-haves and save it, so new homes come to you. When you are ready to see homes in person, my page on how I help buyers walks through each step, from the first tour to closing day.

Already own near downtown and wondering what your home is worth this season? See an instant home value, and I will fine-tune the number for you. Or get in touch or call (239) 300-1427, and let's talk about what you want your day to look like.